A woman in her 20s from the Bay Area asks, “Have you ever seen people successfully use upcoming OKCupid dates as a negotiating tactic to get someone in real life to date them? I know it sounds like a terrible idea, but maybe if done right it could move someone from the friend zone into the dating zone on a semi-subconscious level by sparking their interest and making them realize it’s a now or never type opportunity?”
I’ve had a crush on Eva since we met in junior high. That was 1982, and we’re now in our mid-forties. We attended high school together and stayed in touch periodically in college. Then a long period of time passed until we reconnected through Facebook. We were each married to other people with families of our own.
Shortly after reconnecting online, a mutual friend flew both Eva and me out to his city for his 40th birthday. This was the first time we’d seen each other in person for 15 years! On the last night of this week-long trip, I entered her bedroom and sat next to her and flirted and massaged her, and sparks began to fly. We didn’t do anything sexual then, but we continued to see each other once we’d returned to our normal lives, and soon enough we were having an affair.
As the affair and our feelings for each other deepened, my marriage was slipping away. On four separate occasions, Eva and I “broke up, ” but each time, we would come right back. I divorced, moved out, settling parenting responsibilities with my ex-wife, and finally accepted that I’d fallen in love with Eva. We’ve been together now going on five years. We tell each other that we love each other. It’s very passionate, caring and understanding. She is my true love, the love of my life.
But herein lies the dilemma: Eva remains married to her spouse. I give her all of things that are lacking in her lifeless marriage. Her husband discovered our affair and still will not divorce her.
I have a feeling that there will come a day that the urgency inside of me will rise. But I know that this is not my decision to make. It is entirely up to her what she wants to do. Do I just let it go on, or should I demand all of Eva now?
A divorced straight woman in her early 40s wrote, “I love my ex husband, and I’m so sad that we didn’t work out. I would get back together with him now, but he says he’s done. I’m still confused as to why that didn’t work out. We both love each other so much. I have been dating a lot for two years now, and I have yet to find a guy that I really connect with. I wonder if I’m doomed to be single my whole life now that I’ve lost my ex husband. Do you have any advice to give me other than ‘soldier on and I’ll eventually meet someone’?” We do, of course, have some advice, and the writer included a link to her OKCupid profile, which figures into our response.
A 46 year-old male writes about being in a relationship for almost 10 years with a women who is just “not into sex.” He, on the other hand, likes his sex … a lot. He likes it frequent, kinky, varied, and with different partners. For most of the relationship, he has been getting his needs met elsewhere. Meanwhile, his partner has placed lots of restrictions about where, when, and how they have sex together, and she has not been positive about the idea of an open relationship. He says they are deeply in love, and he feels like shit for cheating. What are his options now?
“I disclose my HSV2 (genital herpes) status in my dating profile. I was getting many messages before putting the HSV2 on there, and I’m still getting many messages, only now at least I have a sense of freedom and honesty. I hope it will help me filter the boys from the men, though I’m not entirely sure it’s helping. Do you think it is wise to be as honest as I am?”
A married woman in an open relationship struggles with how to handle the most important man in her life who isn’t her husband: he’s her coworker, best friend, and her husband’s friend. They started hanging out and making out two years before when he was in an abusive relationship, but they never had sex at his insistence. Even though he has since broken up with his girlfriend, they make out but haven’t had sex. They’ve both declared their love for each other, but it causes her pain when he makes out with her but refuses to consummate the relationship. Even worse, he blames her for the situation when he pulls away, only to resume flirting and wooing her. Her friends say that he is either “playing me, really messed up from his bad relationship, or just a drunk. I would love your take on a) his inconsistent behavior and b) whether I should try to have a calm conversation with him about our friendship, or just go with the flow.”
“I’m currently fooling around and flirting with a few guys. I’m newly single and having a lot of fun. I sometimes wonder if monogamous relationships are just not for me. I tried it and I get bored really easily. I like getting a lot of attention and I get frustrated with just one guy. I feel like there’s no way one guy can give me all the attention I crave. Is this just a phase because I’m young and selfish or is this just me?”
A woman in her early twenties from the New York suburbs wrote in the heat of the moment that, “I was about to text this guy that I have been having casual sex with for the last three months, several times a week, and tell him I need to stop. We met online. He is 10 years older than I am, and I think I may be developing feelings for him, although I try and act cold and detached. I have a lot of other specifics, but I don’t want to bombard you. It was just super weird that I came across you just now.”
“I was in a FWB situation for almost 8 months with this guy. We never went on real dates and mostly met at his drum studio or apartment, talked, and had sex. For me anyway, it was a rare intellectual connection combined with great chemistry. Sex was great, conversations were great, and time passed so quickly with hi. He was not OK with the polyamorous thing and didn’t want to get emotionally involved but was OK with having sex since it was out in the open. I was OK with simply enjoying the times we had together. So, that was working well until one day he just dropped out in the middle of rescheduling one of our meetups because the schedule that day didn’t work out. Like all of a sudden, gone. To this day I’m just still extremely puzzled by this. I’ve moved on and I’m not mad or anything, but just deeply curious. Like, what the hell happened?”
“Maybe you can give me some tips on how to find a girl to join my boyfriend and me.” So says a Brooklyn woman in a three-and-a-half year relationship that she describes as open. Maybe we know voodoo and spells too. That’s not sarcastic; we just might. Regardless, the hunt for the elusive unicorn is on. In case you don’t know, the unicorn is that rare, magical bisexual woman who will jump into bed with with a couple and help them fulfill their fantasies.
Our first message from this fellow was a sarcastic, “What would your advice be for me, being 40, bald, a minority, and despite being ‘a great guy,’ having trouble finding someone I genuinely connect with?” Were we talking to Montel Williams? The angry ghost of Gandhi? He then wrote back a story of a date that led to the dreaded “let’s be friends.” Now he feels a connection and isn’t sure whether he should stick with the great, albeit new, friendship or push for something more.
“Opinions are like babies and puppies. People think their own are the greatest, cutest, most wonderful things in the world. Everyone else finds them annoying and wants you to keep them away … until they want them to play.” So I guess this site is for those who want to ooh and ahh out our (non-biological) babies or play fetch with our puppies, at least for a few minutes. What we’ve been excited to find out is that you’re taking our advice, which is amazing. So they really are cute!?
A 38 year-old male Manhattanite “found out my wife cheated on me with at least two different guys. She didn’t want to talk to me about it, and it drove me nuts. I got angry and for months was verbally angry with her. She had enough and told me she didn’t want me anymore because of my anger. We have two kids, and now I am hanging on to my family with everything I have.”
A 26 year-old Brooklyn woman writes, “I love that I’m surrounded by so many smart and ambitious women in New York, but unfortunately that means we’re all in competition for the same six manchildren. The dudes on OKCupid (and maybe NYC?) are flaky as hell, and I’m tired of having a few great dates where things click, and then nothing. I sort of suspect that the only way I’ll end up in a good long-term relationship is if I leave NYC. I’d be very curious if you two think there’s something I could change about my approach or perspective!”
Most of my sexual experiences have been fairly vanilla. Of my two main long term partners, one would not consider any kink, and the other made me feel strange if I wanted to try anything different and didn’t let me know what she wanted to experience either. Now I kind of have a hang up regarding sex, in that I don’t feel comfortable pushing forward with something non-vanilla, even if it excites me. Also, I am completely uncomfortable if I am not the aggressor. How can I get over both these things?
A 41 year-old divorced woman who does not, to our knowledge, tango or live in Paris writes, “I identify as a sex-positive, joyful and mature person who was married for a long time and has recently re-entered the dating scene. I had a hot tryst while on a work trip abroad that unlocked some unknown erotic treasure trove in me. There was nothing this guy could do wrong, and it kind of made me into a desiring machine. Tried as I did to forget and replace this lover, nothing came close to that voltage generated by us. There is no long term potential with that man (we both have kids from previous relationships who we are committed to loving and prioritizing), but the dialog continues at a leisurely pace. Should I just cut this off, stop obsessing about him to clear space for new partners to come into my life, or continue to patiently nourish a situation I felt was so unique and precious? Is there such a thing as an ideal pheromone match?”
A 35 year-old straight man in New York City writes, “I am very troubled by a terrible realization: I am sexually attracted to immature, naive women who do not qualify for a real girlfriend.” He left a long-term girlfriend for a hot, younger woman whom he couldn’t respect, and now he’s dating another woman whom he likes but doesn’t find sexually appealing. “Following the old French adage, it seems as if my brain is split between La maman et la putain (the mother and the whore). I want to fall in love with a smart woman who cares for me, but those same qualities seem to be a turn off. I am caught between hot women I want to fuck and the well-rounded and caring women who fail to arouse my desire.”
A 38 year-old single woman with a kid writes, “Would it be possible to have you take a look at my OKCupid profile and hypothesize why I keep getting guys who are upfront from the beginning that they aren’t looking for a something long-term? They say they’re monogamish, busy, etc. I’m interested in, though not desperate for, a life partner. I also find many of the men who message me are far older than I am and/or from out of state. Neither of those things is particularly interesting to me.”
A 30 year-old man writes that his wife is stealing his Adderall. They have two small children, whom she takes care of during the day while he works. She also runs a freelance business almost full-time, which frequently keeps her up late. The husband has a prescription for the pills, but he only uses them occasionally and then to help him work. He has noticed pills missing from his prescription bottle for three months in a row. Most recently, he had only used 2 out of 30 pills in a month, and there were only 7 left in the bottle. He asked her if she knew about this, and she claimed to have no idea. She suggested that maybe a workman stole some. He feels bad because he advised her to try Adderall in the first place to help with work. “I’m torn between wanting to bust her for her lying and trying to figure out how serious this is. How do I confront her?”
A 47 year-old straight guy in a rural area is new to dating because he’s shy. “The one relationship I had after high school was because she was the aggressor. That was back in ’87, and it lasted about a year and half. I fear putting sexual information in my dating profile. Like, I fear I may be sitting in front of a potential employer or even my current employer or fellow employees and they start laughing and say ‘So, I see you like to have your women’s genitals clean shaven?’ or ‘So, you love to give head to women?’”
A 42 year-old straight male who cross-dresses, is only interested in women, and only wants an LTR writes, “I’m stuck with a paradox: I have discovered that if I am not perceived as forthright from the start (I don’t always dress up, just like women don’t always dress up), the revelation of what makes me different can be off-putting. On the other hand, if I put who I am out there from the start, no one picks me. OKCupid has in the past provided women who pick me and that has been extremely rewarding. How can I increase my ability to find women who would want, not merely accept what makes me different?”